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(S)-Malic acid forms a salt with N,N′-dimethylpiperazine, [MeN(CH2CH2)2NMe]H22+·2C4H5O5 (1) (triclinic, P1, Z′ = 1), in which the cations link pairs of hydrogen-bonded anion chains to form a molecular ladder. With 4,4′-bipyridyl, (S)-malic acid forms a 1:1 adduct which crystallizes from methanol to yield two polymorphs, (2) (triclinic, P1, Z′ = 1) and (3) (monoclinic, C2, Z′ = 1), while racemic malic acid with 4,4′-bipyridyl also forms a 1:1 adduct, (4) (monoclinic, P21/c, Z′ = 1). In each of (2), (3) and (4) the components are linked by O—H...N and N—H...O into chains of alternating bipyridyl and malate units, which are linked into sheets by O—H...O hydrogen bonds. In each of the 1:1 adducts (5) and (6), formed by, respectively, (S)-malic acid and racemic malic acid with 1,2-bis(4′-pyridyl)ethene, the diamine is disordered over two sets of sites, related by a 180° rotation about the N...N vector. In (5), (C12H10N2)H+·C4H5O5 (triclinic, P1, Z′ = 1), the components are again linked by a combination of N—H...O and O—H...O hydrogen bonds into sheets, while in (6) (triclinic, P{\overline 1}, Z′ = 0.5) there is only partial transfer of the H atom from O to N and the malate component is disordered across a centre of inversion. With 1,4-diazabicyclo[2.2.2]octane, racemic malic acid forms a 1:2 salt, [(C6H12N2)H2]2+·2C4H5O5 (7) (monoclinic, P21/c, Z′ = 2), while (S)-malic acid forms a 1:1 adduct, (8) (monoclinic, P21, Z′ = 3). There are thus six independent molecular components in each. In (7) the ions are linked by an extensive series of N—H...O and O—H...O hydrogen bonds into a three-dimensional framework, but in (8) there is extensive disorder involving all six components, and no refinement proved to be feasible.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102000642/na0134sup1.cif
Contains datablocks global, 1, 2, 3, 4, 5, 6, 7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01341sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01342sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01343sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01344sup5.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01345sup6.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01346sup7.hkl
Contains datablock 6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768102000642/na01347sup8.hkl
Contains datablock 7

CCDC references: 188104; 188105; 188106; 188107; 188108; 188109; 188110

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999).

(1) N,N'-Dimethylpiperazine–(S)-malic acid (1/2) top
Crystal data top
C6H16N2·2(C4H5O5)Z = 1
Mr = 382.37F(000) = 204
Triclinic, P1Dx = 1.426 Mg m3
a = 5.8757 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8751 (4) ÅCell parameters from 1913 reflections
c = 10.6165 (7) Åθ = 2.8–27.6°
α = 70.345 (2)°µ = 0.12 mm1
β = 74.500 (2)°T = 293 K
γ = 87.435 (3)°Plate, colourless
V = 445.24 (4) Å30.35 × 0.27 × 0.13 mm
Data collection top
Kappa-CCD
diffractometer
2041 independent reflections
Radiation source: fine-focus sealed X-ray tube1476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
φ scans, and ω scans with κ offsetsθmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 07
Tmin = 0.959, Tmax = 0.984k = 1010
6309 measured reflectionsl = 1213
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0602P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2041 reflectionsΔρmax = 0.19 e Å3
242 parametersΔρmin = 0.15 e Å3
3 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.106 (18)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. Mean-plane data from the final SHELXL97 refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

0.2346 (0.0116) x + 7.8176 (0.0018) y + 2.3720 (0.0191) z = 3.9234 (0.0179)

* 0.0112 (0.0029) C11 * -0.0031 (0.0008) C12 * -0.0042 (0.0011) O11 * -0.0039 (0.0010) O12

Rms deviation of fitted atoms = 0.0065

- 0.6617 (0.0248) x + 7.0762 (0.0051) y - 1.1634 (0.0150) z = 0.3924 (0.0176)

Angle to previous plane (with approximate e.s.d.) = 19.57 (0.13)

* 0.1204 (0.0015) C11 * -0.3060 (0.0025) C12 * 0.3267 (0.0024) C13 * -0.1410 (0.0013) C14

Rms deviation of fitted atoms = 0.2423

- 2.0854 (0.0128) x + 7.0585 (0.0089) y + 0.2080 (0.0258) z = 1.8413 (0.0335)

Angle to previous plane (with approximate e.s.d.) = 18.48 (0.26)

* 0.0030 (0.0009) C13 * -0.0103 (0.0030) C14 * 0.0035 (0.0010) O13 * 0.0038 (0.0011) O14

Rms deviation of fitted atoms = 0.0059

- 1.0912 (0.0101) x + 7.2585 (0.0056) y - 0.3458 (0.0188) z = 4.1292 (0.0141)

Angle to previous plane (with approximate e.s.d.) = 11.75 (0.22)

* 0.0089 (0.0025) C21 * -0.0025 (0.0007) C22 * -0.0033 (0.0009) O21 * -0.0031 (0.0009) O22

Rms deviation of fitted atoms = 0.0051

0.4287 (0.0252) x + 7.7524 (0.0034) y + 1.9225 (0.0158) z = 6.0610 (0.0200)

Angle to previous plane (with approximate e.s.d.) = 17.20 (0.15)

* 0.1314 (0.0014) C21 * -0.3302 (0.0025) C22 * 0.3466 (0.0027) C23 * -0.1477 (0.0015) C24

Rms deviation of fitted atoms = 0.2589

0.9739 (0.0126) x + 6.8995 (0.0080) y - 1.0125 (0.0234) z = 6.4349 (0.0099)

Angle to previous plane (with approximate e.s.d.) = 18.77 (0.18)

* 0.0039 (0.0010) C23 * -0.0134 (0.0035) C24 * 0.0044 (0.0011) O23 * 0.0051 (0.0013) O24

Rms deviation of fitted atoms = 0.0077

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.1017 (4)0.2619 (4)0.7792 (2)0.0531 (7)
O120.1490 (4)0.2068 (4)0.9857 (3)0.0618 (8)
O130.1483 (5)0.1815 (4)1.2248 (3)0.0660 (8)
O140.1033 (6)0.2531 (5)1.3185 (3)0.0791 (10)
O150.4739 (4)0.2495 (4)0.8703 (2)0.0543 (7)
C110.0599 (6)0.2269 (5)0.9051 (4)0.0406 (8)
C120.2603 (5)0.1972 (5)0.9771 (3)0.0379 (7)
C130.2426 (6)0.3012 (5)1.0762 (3)0.0443 (8)
C140.0591 (7)0.2410 (5)1.2163 (4)0.0457 (9)
O210.9097 (4)0.7161 (4)0.2286 (3)0.0514 (7)
O221.1659 (4)0.7450 (3)0.0268 (3)0.0438 (6)
O231.1703 (4)0.7377 (4)0.2070 (3)0.0621 (8)
O240.9014 (6)0.7595 (5)0.3180 (3)0.0743 (10)
O250.5447 (4)0.7033 (5)0.1388 (3)0.0622 (8)
C210.9589 (5)0.7193 (4)0.1065 (3)0.0342 (7)
C220.7605 (5)0.6852 (5)0.0484 (3)0.0388 (7)
C230.7780 (5)0.8086 (5)0.1011 (3)0.0427 (7)
C240.9540 (6)0.7641 (5)0.2180 (4)0.0464 (9)
N10.4785 (5)0.6850 (4)0.4166 (3)0.0403 (7)
N40.5214 (5)0.3149 (4)0.5834 (3)0.0437 (7)
C20.2957 (6)0.5420 (5)0.4492 (4)0.0435 (8)
C30.4014 (7)0.3610 (5)0.4704 (4)0.0460 (9)
C50.7014 (6)0.4597 (5)0.5537 (4)0.0475 (9)
C60.5962 (6)0.6408 (5)0.5317 (4)0.0478 (9)
C70.3747 (8)0.8657 (6)0.3894 (5)0.0652 (12)
C80.6309 (8)0.1370 (6)0.6045 (4)0.0646 (12)
H130.15060.17561.14940.099*
H150.58410.24710.90460.081*
H12A0.26150.06811.02860.045*
H13A0.21450.42541.02770.053*
H13B0.39630.30171.09370.053*
H231.18140.75480.13670.093*
H250.44010.71930.09870.093*
H22A0.76600.56000.04990.047*
H23A0.62250.80880.11650.051*
H23B0.81690.93050.10840.051*
H10.58970.68610.33800.048*
H40.41080.30890.66360.052*
H2A0.22160.56940.37370.052*
H2B0.17470.53880.53260.052*
H3A0.27770.26950.49330.055*
H3B0.51460.36180.38490.055*
H5A0.82550.46370.47130.057*
H5B0.77210.43190.63060.057*
H6A0.48130.64050.61660.057*
H6B0.71960.73250.50910.057*
H7A0.26610.87110.47330.098*
H7B0.29230.88480.31930.098*
H7C0.49870.95760.35810.098*
H8A0.73990.13720.51910.097*
H8B0.50970.04340.63350.097*
H8C0.71380.11540.67470.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0340 (14)0.094 (2)0.0326 (16)0.0004 (12)0.0101 (11)0.0210 (13)
O120.0277 (14)0.120 (2)0.0406 (16)0.0036 (14)0.0075 (11)0.0312 (15)
O130.0463 (17)0.116 (2)0.0355 (15)0.0174 (15)0.0021 (12)0.0288 (15)
O140.067 (2)0.141 (3)0.0486 (18)0.0042 (18)0.0172 (15)0.0554 (19)
O150.0291 (14)0.101 (2)0.0328 (15)0.0007 (13)0.0055 (11)0.0238 (13)
C110.0322 (19)0.056 (2)0.0351 (19)0.0007 (14)0.0082 (15)0.0173 (14)
C120.0299 (15)0.0521 (19)0.0288 (16)0.0049 (13)0.0050 (12)0.0127 (14)
C130.0393 (16)0.057 (2)0.0399 (18)0.0003 (14)0.0116 (13)0.0201 (15)
C140.045 (2)0.062 (2)0.036 (2)0.0085 (16)0.0134 (15)0.0230 (16)
O210.0395 (15)0.0864 (18)0.0327 (15)0.0006 (12)0.0118 (11)0.0237 (12)
O220.0289 (13)0.0655 (15)0.0386 (14)0.0017 (10)0.0090 (10)0.0196 (11)
O230.0380 (14)0.109 (2)0.0451 (17)0.0148 (15)0.0070 (12)0.0380 (16)
O240.063 (2)0.129 (3)0.0429 (18)0.0071 (17)0.0163 (15)0.0428 (18)
O250.0261 (13)0.131 (2)0.0306 (14)0.0009 (14)0.0066 (11)0.0280 (14)
C210.0295 (17)0.0423 (17)0.0292 (17)0.0032 (12)0.0080 (13)0.0103 (12)
C220.0289 (15)0.0534 (19)0.0322 (16)0.0018 (13)0.0071 (12)0.0126 (14)
C230.0330 (14)0.063 (2)0.0333 (16)0.0060 (14)0.0112 (12)0.0164 (14)
C240.0382 (19)0.065 (2)0.0340 (19)0.0025 (16)0.0091 (15)0.0149 (15)
N10.0300 (14)0.0571 (17)0.0318 (15)0.0021 (12)0.0013 (11)0.0174 (12)
N40.0424 (17)0.0572 (18)0.0291 (15)0.0027 (13)0.0059 (12)0.0143 (12)
C20.0295 (18)0.064 (2)0.0348 (19)0.0036 (14)0.0056 (15)0.0152 (15)
C30.048 (2)0.060 (2)0.033 (2)0.0056 (17)0.0127 (16)0.0167 (15)
C50.0302 (18)0.078 (3)0.0326 (19)0.0056 (16)0.0090 (15)0.0155 (16)
C60.0386 (19)0.072 (2)0.035 (2)0.0124 (16)0.0056 (15)0.0235 (17)
C70.068 (3)0.064 (3)0.053 (3)0.011 (2)0.002 (2)0.018 (2)
C80.071 (3)0.070 (3)0.042 (2)0.017 (2)0.003 (2)0.0155 (18)
Geometric parameters (Å, º) top
O11—C111.227 (4)C23—H23B0.97
O12—C111.276 (4)N1—C21.480 (4)
O13—C141.295 (5)N1—C71.490 (5)
O13—H130.82N1—C61.496 (5)
O14—C141.215 (5)N1—H10.91
O15—C121.415 (4)N4—C51.485 (5)
O15—H150.82N4—C31.485 (5)
C11—C121.537 (5)N4—C81.488 (5)
C12—C131.518 (4)N4—H40.91
C12—H12A0.98C2—C31.499 (5)
C13—C141.521 (5)C2—H2A0.97
C13—H13A0.97C2—H2B0.97
C13—H13B0.97C3—H3A0.97
O21—C211.242 (4)C3—H3B0.97
O22—C211.262 (4)C5—C61.499 (5)
O23—C241.308 (5)C5—H5A0.97
O23—H230.82C5—H5B0.97
O24—C241.194 (5)C6—H6A0.97
O25—C221.405 (4)C6—H6B0.97
O25—H250.82C7—H7A0.96
C21—C221.528 (5)C7—H7B0.96
C22—C231.536 (4)C7—H7C0.96
C22—H22A0.98C8—H8A0.96
C23—C241.519 (4)C8—H8B0.96
C23—H23A0.97C8—H8C0.96
C14—O13—H13109.5C7—N1—H1108.0
C12—O15—H15109.5C6—N1—H1108.0
O11—C11—O12123.3 (3)C5—N4—C3109.9 (3)
O11—C11—C12121.3 (3)C5—N4—C8110.6 (3)
O12—C11—C12115.3 (3)C3—N4—C8112.1 (3)
O15—C12—C13109.7 (3)C5—N4—H4108.0
O15—C12—C11106.5 (3)C3—N4—H4108.0
C13—C12—C11114.6 (2)C8—N4—H4108.0
O15—C12—H12A108.6N1—C2—C3111.0 (3)
C13—C12—H12A108.6N1—C2—H2A109.4
C11—C12—H12A108.6C3—C2—H2A109.4
C12—C13—C14119.9 (3)N1—C2—H2B109.4
C12—C13—H13A107.4C3—C2—H2B109.4
C14—C13—H13A107.4H2A—C2—H2B108.0
C12—C13—H13B107.4N4—C3—C2111.3 (3)
C14—C13—H13B107.4N4—C3—H3A109.4
H13A—C13—H13B106.9C2—C3—H3A109.4
O14—C14—O13120.1 (4)N4—C3—H3B109.4
O14—C14—C13120.7 (4)C2—C3—H3B109.4
O13—C14—C13119.1 (3)H3A—C3—H3B108.0
C24—O23—H23109.5N4—C5—C6111.8 (3)
C22—O25—H25109.5N4—C5—H5A109.2
O21—C21—O22124.0 (3)C6—C5—H5A109.2
O21—C21—C22118.9 (3)N4—C5—H5B109.2
O22—C21—C22117.0 (3)C6—C5—H5B109.2
O25—C22—C21107.6 (3)H5A—C5—H5B107.9
O25—C22—C23110.8 (2)N1—C6—C5110.5 (3)
C21—C22—C23114.3 (3)N1—C6—H6A109.5
O25—C22—H22A108.0C5—C6—H6A109.5
C21—C22—H22A108.0N1—C6—H6B109.5
C23—C22—H22A108.0C5—C6—H6B109.5
C24—C23—C22117.8 (3)H6A—C6—H6B108.1
C24—C23—H23A107.9N1—C7—H7A109.5
C22—C23—H23A107.9N1—C7—H7B109.5
C24—C23—H23B107.9H7A—C7—H7B109.5
C22—C23—H23B107.9N1—C7—H7C109.5
H23A—C23—H23B107.2H7A—C7—H7C109.5
O24—C24—O23121.1 (4)H7B—C7—H7C109.5
O24—C24—C23122.1 (3)N4—C8—H8A109.5
O23—C24—C23116.8 (3)N4—C8—H8B109.5
C2—N1—C7110.8 (3)H8A—C8—H8B109.5
C2—N1—C6109.4 (3)N4—C8—H8C109.5
C7—N1—C6112.4 (3)H8A—C8—H8C109.5
C2—N1—H1108.0H8B—C8—H8C109.5
O11—C11—C12—O1510.1 (4)C21—C22—C23—C2478.1 (4)
O12—C11—C12—O15172.1 (3)C22—C23—C24—O24132.3 (4)
O11—C11—C12—C13131.6 (3)C22—C23—C24—O2350.4 (5)
O12—C11—C12—C1350.6 (4)C7—N1—C2—C3177.5 (3)
O15—C12—C13—C14166.3 (3)C6—N1—C2—C358.0 (3)
C11—C12—C13—C1473.9 (4)C5—N4—C3—C255.6 (4)
C12—C13—C14—O14143.7 (4)C8—N4—C3—C2179.0 (3)
C12—C13—C14—O1338.3 (5)N1—C2—C3—N458.0 (4)
O21—C21—C22—O2515.5 (4)C3—N4—C5—C655.6 (4)
O22—C21—C22—O25166.2 (3)C8—N4—C5—C6179.9 (3)
O21—C21—C22—C23139.1 (3)C2—N1—C6—C557.3 (3)
O22—C21—C22—C2342.6 (4)C7—N1—C6—C5179.0 (3)
O25—C22—C23—C24160.1 (3)N4—C5—C6—N157.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O120.821.672.480 (4)169
O15—H15···O12i0.821.952.763 (4)172
O23—H23···O220.821.692.494 (4)167
O25—H25···O22ii0.821.942.751 (3)173
N1—H1···O210.911.902.736 (4)151
N1—H1···O250.912.162.824 (4)129
N4—H4···O110.911.872.710 (4)152
N4—H4···O150.912.212.849 (4)126
C6—H6A···O23iii0.972.543.476 (5)163
C7—H7A···O24iii0.962.573.453 (6)153
C7—H7C···O13iv0.962.553.489 (6)167
C8—H8A···O14v0.962.523.408 (5)153
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x1, y, z+1; (iv) x+1, y+1, z1; (v) x+1, y, z1.
(2) 4,4'-Bipyridyl–(S)-malic acid (1/1),triclinic polymorph top
Crystal data top
C10H8.5N2·C4H5.5O5Z = 1
Mr = 290.27F(000) = 152
Triclinic, P1Dx = 1.491 Mg m3
a = 5.1647 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.2749 (5) ÅCell parameters from 1351 reflections
c = 10.2126 (9) Åθ = 3.7–27.4°
α = 83.235 (3)°µ = 0.12 mm1
β = 89.808 (3)°T = 150 K
γ = 79.601 (3)°Block, colourless
V = 323.21 (5) Å30.40 × 0.30 × 0.30 mm
Data collection top
Kappa-CCD
diffractometer
1465 independent reflections
Radiation source: fine-focus sealed X-ray tube1195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ scans, and ω scans with κ offsetsθmax = 27.4°, θmin = 3.7°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 06
Tmin = 0.956, Tmax = 0.966k = 78
3702 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0823P)2 + 0.0245P]
where P = (Fo2 + 2Fc2)/3
1465 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.41 e Å3
3 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.4999 (4)0.5001 (4)0.4999 (3)0.0299 (6)
O20.5276 (5)0.1762 (4)0.6218 (3)0.0370 (7)
O30.0331 (4)0.0958 (4)0.3020 (2)0.0302 (6)
O40.1493 (5)0.1301 (4)0.1360 (2)0.0345 (6)
O50.0886 (5)0.4473 (4)0.3617 (3)0.0411 (7)
C10.4325 (7)0.3122 (6)0.5305 (3)0.0251 (8)
C20.2265 (6)0.2619 (5)0.4367 (3)0.0249 (8)
C30.3680 (6)0.1000 (6)0.3468 (3)0.0259 (8)
C40.1730 (6)0.0464 (5)0.2506 (3)0.0253 (8)
N110.8519 (6)0.5652 (5)0.6578 (3)0.0257 (6)
N211.7390 (6)0.7974 (5)1.1249 (3)0.0264 (6)
C120.9171 (7)0.4272 (6)0.7682 (4)0.0286 (8)
C131.0959 (7)0.4635 (6)0.8609 (4)0.0283 (8)
C141.2095 (6)0.6499 (6)0.8391 (3)0.0228 (7)
C151.1430 (7)0.7881 (6)0.7232 (3)0.0279 (8)
C160.9630 (7)0.7417 (6)0.6354 (3)0.0278 (8)
C221.6992 (6)0.9162 (6)1.0073 (4)0.0272 (8)
C231.5299 (7)0.8738 (6)0.9119 (3)0.0266 (8)
C241.3973 (6)0.6992 (6)0.9383 (3)0.0231 (7)
C251.4408 (7)0.5763 (6)1.0613 (4)0.0295 (8)
C261.6124 (7)0.6289 (7)1.1515 (4)0.0312 (9)
H10.61020.51870.55580.045*0.50
H30.05520.13210.24210.045*
H50.14390.55800.38060.062*
H20.09740.18970.49050.030*
H3A0.50620.16430.29740.031*
H3B0.45380.03540.40100.031*
H110.73720.53940.60090.031*0.50
H120.83860.30100.78350.034*
H131.14010.36290.93800.034*
H151.22060.91420.70420.034*
H160.91740.83840.55680.033*
H221.79011.03460.98780.033*
H231.50490.96300.82940.032*
H251.35320.45661.08360.035*
H261.64130.54271.23490.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0338 (13)0.0276 (13)0.0302 (14)0.0129 (10)0.0120 (10)0.0003 (10)
O20.0480 (16)0.0339 (15)0.0307 (15)0.0169 (13)0.0153 (12)0.0054 (12)
O30.0375 (14)0.0338 (15)0.0233 (13)0.0186 (11)0.0111 (10)0.0007 (10)
O40.0467 (15)0.0366 (15)0.0237 (13)0.0199 (12)0.0068 (11)0.0022 (11)
O50.0416 (14)0.0304 (13)0.0508 (17)0.0042 (11)0.0169 (12)0.0054 (12)
C10.0285 (17)0.0284 (19)0.0204 (18)0.0090 (14)0.0023 (13)0.0054 (15)
C20.0248 (16)0.0241 (17)0.0272 (19)0.0078 (14)0.0034 (13)0.0031 (14)
C30.0258 (17)0.0280 (19)0.0251 (18)0.0073 (15)0.0080 (13)0.0043 (14)
C40.0261 (17)0.0230 (18)0.028 (2)0.0056 (14)0.0046 (14)0.0046 (15)
N110.0265 (13)0.0295 (16)0.0232 (15)0.0095 (12)0.0049 (11)0.0049 (12)
N210.0271 (14)0.0307 (16)0.0231 (15)0.0107 (12)0.0048 (11)0.0019 (12)
C120.0354 (19)0.0271 (18)0.0258 (19)0.0136 (15)0.0076 (14)0.0011 (15)
C130.0341 (18)0.0288 (18)0.0233 (18)0.0109 (15)0.0092 (14)0.0000 (14)
C140.0226 (15)0.0280 (18)0.0184 (17)0.0057 (14)0.0021 (12)0.0038 (13)
C150.0286 (16)0.032 (2)0.025 (2)0.0127 (15)0.0046 (14)0.0018 (16)
C160.0294 (17)0.0305 (19)0.0252 (19)0.0116 (15)0.0064 (13)0.0008 (15)
C220.0272 (17)0.0301 (18)0.026 (2)0.0110 (14)0.0045 (13)0.0028 (15)
C230.0312 (17)0.0291 (19)0.0210 (18)0.0115 (14)0.0034 (13)0.0001 (14)
C240.0225 (15)0.0256 (17)0.0228 (17)0.0071 (13)0.0039 (12)0.0045 (14)
C250.0333 (18)0.0297 (19)0.028 (2)0.0159 (16)0.0084 (14)0.0032 (15)
C260.0341 (19)0.039 (2)0.023 (2)0.0147 (17)0.0073 (14)0.0014 (16)
Geometric parameters (Å, º) top
O1—C11.292 (4)N21—C261.341 (5)
O1—H10.84C12—C131.391 (5)
O2—C11.226 (4)C12—H120.95
O3—C41.309 (4)C13—C141.395 (5)
O3—H30.84C13—H130.95
O4—C41.222 (4)C14—C151.387 (5)
O5—C21.394 (4)C14—C241.501 (4)
O5—H50.84C15—C161.385 (5)
C1—C21.532 (4)C15—H150.95
C2—C31.535 (4)C16—H160.95
C2—H21.00C22—C231.391 (5)
C3—C41.516 (5)C22—H220.95
C3—H3A0.99C23—C241.393 (5)
C3—H3B0.99C23—H230.95
N11—C161.333 (5)C24—C251.391 (5)
N11—C121.342 (5)C25—C261.388 (5)
N11—H110.88C25—H250.95
N21—C221.333 (5)C26—H260.95
C1—O1—H1109.5C12—C13—C14119.0 (3)
C4—O3—H3109.5C12—C13—H13120.5
C2—O5—H5109.5C14—C13—H13120.5
O2—C1—O1125.2 (3)C15—C14—C13118.0 (3)
O2—C1—C2120.5 (3)C15—C14—C24121.1 (3)
O1—C1—C2114.2 (3)C13—C14—C24120.9 (3)
O5—C2—C1113.3 (3)C16—C15—C14119.8 (4)
O5—C2—C3110.5 (3)C16—C15—H15120.1
C1—C2—C3108.0 (2)C14—C15—H15120.1
O5—C2—H2108.3N11—C16—C15121.9 (3)
C1—C2—H2108.3N11—C16—H16119.0
C3—C2—H2108.3C15—C16—H16119.0
C4—C3—C2110.2 (2)N21—C22—C23122.7 (4)
C4—C3—H3A109.6N21—C22—H22118.7
C2—C3—H3A109.6C23—C22—H22118.7
C4—C3—H3B109.6C22—C23—C24119.4 (3)
C2—C3—H3B109.6C22—C23—H23120.3
H3A—C3—H3B108.1C24—C23—H23120.3
O4—C4—O3123.6 (3)C25—C24—C23117.4 (3)
O4—C4—C3122.6 (3)C25—C24—C14121.4 (3)
O3—C4—C3113.8 (3)C23—C24—C14121.1 (3)
C16—N11—C12119.2 (3)C26—C25—C24119.9 (4)
C16—N11—H11120.4C26—C25—H25120.1
C12—N11—H11120.4C24—C25—H25120.1
C22—N21—C26118.5 (3)N21—C26—C25122.2 (3)
N11—C12—C13122.0 (3)N21—C26—H26118.9
N11—C12—H12119.0C25—C26—H26118.9
C13—C12—H12119.0
O2—C1—C2—O5164.0 (3)C12—N11—C16—C150.4 (5)
O1—C1—C2—O519.0 (4)C14—C15—C16—N110.7 (6)
O2—C1—C2—C373.3 (4)C26—N21—C22—C230.7 (5)
O1—C1—C2—C3103.6 (3)N21—C22—C23—C240.7 (5)
O5—C2—C3—C455.0 (3)C22—C23—C24—C250.6 (5)
C1—C2—C3—C4179.4 (3)C22—C23—C24—C14179.0 (3)
C2—C3—C4—O4100.7 (4)C15—C14—C24—C25172.2 (4)
C2—C3—C4—O378.9 (3)C13—C14—C24—C257.6 (4)
C16—N11—C12—C130.5 (6)C15—C14—C24—C236.1 (5)
N11—C12—C13—C140.5 (6)C13—C14—C24—C23174.0 (4)
C12—C13—C14—C151.7 (5)C23—C24—C25—C260.5 (5)
C12—C13—C14—C24178.2 (3)C14—C24—C25—C26178.9 (3)
C13—C14—C15—C161.8 (5)C22—N21—C26—C250.6 (6)
C24—C14—C15—C16178.1 (3)C24—C25—C26—N210.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N110.841.712.553 (4)175
O3—H3···N21i0.841.752.588 (4)176
O5—H5···O10.842.162.646 (3)117
O5—H5···O3ii0.842.202.823 (4)131
N11—H11···O10.881.672.553 (4)175
C13—H13···O4iii0.952.353.280 (5)167
C15—H15···O2iv0.952.563.477 (4)163
C23—H23···O2iv0.952.383.324 (4)170
C25—H25···O4iii0.952.473.420 (5)176
Symmetry codes: (i) x2, y1, z1; (ii) x, y+1, z; (iii) x+1, y, z+1; (iv) x+1, y+1, z.
(3) 4,4'-Bipyridyl–(S)-malic acid (1/1), monoclinic polymorph top
Crystal data top
2(C10H8.5N2)·2(C4H5.5O5)F(000) = 608
Mr = 580.54Dx = 1.440 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 20.500 (4) ÅCell parameters from 1263 reflections
b = 4.6656 (9) Åθ = 2.7–25.0°
c = 14.201 (3) ŵ = 0.11 mm1
β = 99.68 (3)°T = 150 K
V = 1338.9 (5) Å3Needle, colourless
Z = 20.25 × 0.12 × 0.12 mm
Data collection top
Kappa-CCD
diffractometer
1343 independent reflections
Radiation source: fine-focus sealed X-ray tube963 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 2324
Tmin = 0.973, Tmax = 0.987k = 54
4367 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0487P)2 + 0.1485P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1343 reflectionsΔρmax = 0.21 e Å3
194 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (3)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.09059 (13)0.5000 (9)0.44330 (18)0.0397 (9)
O20.20025 (13)0.5691 (8)0.48473 (18)0.0344 (9)
O30.16031 (13)0.8164 (9)0.11410 (18)0.0369 (8)
O40.06471 (14)0.9767 (8)0.14985 (19)0.0407 (9)
O50.20213 (15)0.9555 (8)0.34347 (19)0.0397 (9)
C10.1476 (2)0.6085 (11)0.4325 (3)0.0302 (11)
C20.14279 (19)0.8025 (11)0.3460 (2)0.0286 (10)
C30.1256 (2)0.6267 (10)0.2534 (3)0.0304 (11)
C40.1132 (2)0.8241 (11)0.1667 (3)0.0292 (10)
N110.09983 (17)0.1794 (9)0.5896 (2)0.0325 (10)
N210.14390 (17)0.8094 (9)0.9739 (2)0.0333 (10)
C120.1568 (2)0.0436 (11)0.6157 (3)0.0324 (11)
C130.1668 (2)0.1510 (12)0.6907 (3)0.0334 (12)
C140.11619 (19)0.2079 (11)0.7423 (3)0.0273 (10)
C150.0573 (2)0.0593 (12)0.7150 (3)0.0363 (12)
C160.0506 (2)0.1280 (12)0.6385 (3)0.0398 (14)
C220.0889 (2)0.6581 (13)0.9533 (3)0.0404 (13)
C230.0774 (2)0.4598 (13)0.8804 (3)0.0386 (13)
C240.12626 (19)0.4156 (11)0.8245 (3)0.0280 (11)
C250.1840 (2)0.5704 (11)0.8466 (3)0.0304 (11)
C260.1909 (2)0.7639 (11)0.9220 (3)0.0315 (11)
H10.09460.41420.49600.060*
H30.15150.93340.06880.055*0.50
H50.22330.97250.39920.059*
H20.10650.94410.34820.034*
H3A0.16260.49490.24750.037*
H3B0.08570.50970.25590.037*
H210.14910.93611.02050.040*0.50
H120.19210.08110.58190.039*
H130.20820.24560.70680.040*
H150.02160.08640.74900.044*
H160.00950.22370.61990.048*
H220.05530.68760.99090.048*
H230.03700.35560.86850.046*
H250.21880.54520.81070.036*
H260.23110.86810.93710.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0343 (17)0.056 (3)0.0283 (15)0.0098 (18)0.0038 (13)0.0139 (16)
O20.0278 (16)0.044 (2)0.0302 (15)0.0019 (17)0.0014 (13)0.0060 (15)
O30.0314 (16)0.049 (2)0.0323 (16)0.0050 (17)0.0122 (13)0.0131 (16)
O40.0338 (17)0.054 (2)0.0352 (16)0.011 (2)0.0086 (13)0.0153 (17)
O50.0422 (18)0.045 (2)0.0288 (14)0.0165 (17)0.0014 (13)0.0054 (15)
C10.033 (2)0.035 (3)0.025 (2)0.004 (2)0.013 (2)0.001 (2)
C20.024 (2)0.036 (3)0.026 (2)0.004 (2)0.0047 (16)0.002 (2)
C30.032 (2)0.031 (3)0.028 (2)0.003 (2)0.0024 (18)0.005 (2)
C40.030 (2)0.032 (3)0.024 (2)0.006 (3)0.0004 (18)0.003 (2)
N110.028 (2)0.038 (3)0.0312 (19)0.0003 (19)0.0051 (16)0.0062 (18)
N210.032 (2)0.038 (3)0.0294 (18)0.002 (2)0.0036 (16)0.0094 (18)
C120.033 (2)0.036 (3)0.031 (2)0.002 (2)0.0101 (19)0.002 (2)
C130.028 (2)0.036 (3)0.036 (2)0.002 (2)0.0077 (19)0.002 (2)
C140.029 (2)0.028 (3)0.026 (2)0.001 (2)0.0045 (17)0.001 (2)
C150.026 (2)0.044 (3)0.040 (2)0.003 (2)0.0073 (19)0.013 (2)
C160.027 (2)0.050 (4)0.042 (3)0.003 (2)0.003 (2)0.015 (3)
C220.030 (2)0.055 (4)0.039 (3)0.010 (3)0.013 (2)0.014 (2)
C230.030 (2)0.049 (4)0.038 (2)0.006 (3)0.0097 (19)0.015 (3)
C240.026 (2)0.031 (3)0.026 (2)0.001 (2)0.0021 (17)0.002 (2)
C250.024 (2)0.037 (3)0.030 (2)0.002 (2)0.0069 (17)0.005 (2)
C260.029 (2)0.033 (3)0.033 (2)0.001 (2)0.0065 (19)0.001 (2)
Geometric parameters (Å, º) top
O1—C11.306 (5)N21—H210.88
O1—H10.84C12—C131.388 (7)
O2—C11.217 (5)C12—H120.95
O3—C41.318 (5)C13—C141.392 (5)
O3—H30.84C13—H130.95
O4—C41.213 (5)C14—C151.390 (6)
O5—C21.416 (5)C14—C241.505 (6)
O5—H50.84C15—C161.384 (6)
C1—C21.516 (6)C15—H150.95
C2—C31.539 (6)C16—H160.95
C2—H21.00C22—C231.379 (7)
C3—C41.524 (6)C22—H220.95
C3—H3A0.99C23—C241.394 (6)
C3—H3B0.99C23—H230.95
N11—C121.326 (5)C24—C251.378 (6)
N11—C161.340 (5)C25—C261.390 (6)
N21—C221.320 (6)C25—H250.95
N21—C261.325 (5)C26—H260.95
C1—O1—H1109.5C12—C13—C14120.1 (4)
C4—O3—H3109.5C12—C13—H13120.0
C2—O5—H5109.5C14—C13—H13120.0
O2—C1—O1126.1 (4)C15—C14—C13116.6 (4)
O2—C1—C2121.0 (4)C15—C14—C24122.5 (4)
O1—C1—C2112.9 (4)C13—C14—C24120.9 (4)
O5—C2—C1112.5 (3)C16—C15—C14120.1 (4)
O5—C2—C3108.7 (3)C16—C15—H15120.0
C1—C2—C3110.4 (4)C14—C15—H15120.0
O5—C2—H2108.4N11—C16—C15122.4 (4)
C1—C2—H2108.4N11—C16—H16118.8
C3—C2—H2108.4C15—C16—H16118.8
C4—C3—C2110.5 (4)N21—C22—C23123.9 (4)
C4—C3—H3A109.5N21—C22—H22118.0
C2—C3—H3A109.5C23—C22—H22118.0
C4—C3—H3B109.5C22—C23—C24118.5 (4)
C2—C3—H3B109.5C22—C23—H23120.7
H3A—C3—H3B108.1C24—C23—H23120.7
O4—C4—O3124.0 (4)C25—C24—C23117.7 (4)
O4—C4—C3122.3 (4)C25—C24—C14121.0 (4)
O3—C4—C3113.7 (4)C23—C24—C14121.3 (4)
C12—N11—C16118.4 (4)C24—C25—C26119.2 (4)
C22—N21—C26117.7 (4)C24—C25—H25120.4
C22—N21—H21121.2C26—C25—H25120.4
C26—N21—H21121.2N21—C26—C25122.9 (4)
N11—C12—C13122.5 (4)N21—C26—H26118.5
N11—C12—H12118.8C25—C26—H26118.5
C13—C12—H12118.8
O2—C1—C2—O58.7 (6)C12—N11—C16—C150.4 (7)
O1—C1—C2—O5170.3 (4)C14—C15—C16—N111.7 (8)
O2—C1—C2—C3112.9 (5)C26—N21—C22—C231.0 (8)
O1—C1—C2—C368.1 (5)N21—C22—C23—C240.2 (9)
O5—C2—C3—C462.5 (5)C22—C23—C24—C251.0 (7)
C1—C2—C3—C4173.6 (3)C22—C23—C24—C14178.4 (4)
C2—C3—C4—O470.0 (6)C15—C14—C24—C25176.6 (5)
C2—C3—C4—O3108.6 (4)C13—C14—C24—C254.7 (7)
C16—N11—C12—C130.8 (7)C15—C14—C24—C232.8 (7)
N11—C12—C13—C140.7 (7)C13—C14—C24—C23175.8 (5)
C12—C13—C14—C150.6 (7)C23—C24—C25—C260.6 (7)
C12—C13—C14—C24179.3 (4)C14—C24—C25—C26178.8 (4)
C13—C14—C15—C161.7 (7)C22—N21—C26—C251.4 (7)
C24—C14—C15—C16179.6 (4)C24—C25—C26—N210.6 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N110.841.712.541 (5)169
O3—H3···N21i0.841.792.627 (5)173
O5—H5···O20.842.332.702 (4)107
O5—H5···O2ii0.842.122.932 (4)162
N21—H21···O3iii0.881.752.627 (5)179
C15—H15···O4iv0.952.483.403 (5)165
C16—H16···O1v0.952.463.407 (6)173
Symmetry codes: (i) x, y+2, z1; (ii) x+1/2, y+1/2, z+1; (iii) x, y2, z+1; (iv) x, y1, z+1; (v) x, y, z+1.
(4) 4,4'-Bipyridyl–racemic malic acid (1/1) top
Crystal data top
C10H8.5N2·C4H5.5O5F(000) = 608
Mr = 290.27Dx = 1.450 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.1274 (8) ÅCell parameters from 3105 reflections
b = 4.7459 (3) Åθ = 2.7–27.5°
c = 20.1749 (13) ŵ = 0.11 mm1
β = 100.565 (3)°T = 150 K
V = 1329.74 (14) Å3Needle, colourless
Z = 40.28 × 0.12 × 0.12 mm
Data collection top
Kappa-CCD
diffractometer
3029 independent reflections
Radiation source: fine-focus sealed X-ray tube1416 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 018
Tmin = 0.969, Tmax = 0.987k = 06
11155 measured reflectionsl = 2625
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.189 w = 1/[σ2(Fo2) + (0.0815P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3029 reflectionsΔρmax = 0.27 e Å3
194 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.43907 (15)0.5037 (6)0.08902 (10)0.0393 (7)
O20.48186 (15)0.4477 (5)0.20084 (10)0.0363 (6)
O30.11054 (15)0.1783 (6)0.15430 (11)0.0410 (7)
O40.15342 (16)0.0307 (6)0.06572 (11)0.0438 (7)
O50.34279 (15)0.0552 (6)0.20387 (11)0.0401 (7)
C10.4294 (2)0.3980 (8)0.14710 (15)0.0302 (8)
C20.3458 (2)0.1917 (8)0.14221 (16)0.0347 (9)
C30.2508 (2)0.3472 (9)0.12011 (17)0.0401 (9)
C40.1666 (2)0.1444 (8)0.10980 (16)0.0319 (8)
N110.58205 (17)0.8388 (6)0.09907 (12)0.0297 (7)
N210.96865 (18)1.8090 (6)0.13977 (13)0.0325 (7)
C120.6118 (2)0.9651 (7)0.15769 (15)0.0309 (8)
C130.6874 (2)1.1562 (8)0.16752 (15)0.0312 (8)
C140.7341 (2)1.2177 (7)0.11466 (14)0.0263 (8)
C150.7021 (2)1.0815 (8)0.05357 (15)0.0378 (9)
C160.6259 (2)0.8943 (8)0.04748 (15)0.0390 (10)
C220.9463 (2)1.6556 (8)0.08411 (16)0.0360 (9)
C230.8716 (2)1.4607 (8)0.07333 (16)0.0349 (9)
C240.8166 (2)1.4214 (7)0.12356 (14)0.0269 (8)
C250.8402 (2)1.5795 (8)0.18220 (15)0.0316 (8)
C260.9163 (2)1.7683 (7)0.18809 (16)0.0319 (8)
H10.49340.58010.09260.059*0.50
H30.06350.06780.14550.062*
H50.39760.06080.22850.060*
H20.35240.04580.10760.042*
H3A0.24240.48780.15480.048*
H3B0.25230.44910.07750.048*
H110.53370.71910.09420.036*0.50
H120.58040.92350.19430.037*
H130.70701.24410.21010.037*
H150.73251.11700.01610.045*
H160.60430.80320.00550.047*
H220.98341.68030.04970.043*
H230.85811.35600.03250.042*
H250.80481.55870.21770.038*
H260.93221.87440.22850.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0366 (13)0.0521 (19)0.0296 (12)0.0191 (12)0.0071 (10)0.0044 (11)
O20.0295 (11)0.0476 (18)0.0308 (12)0.0062 (11)0.0027 (10)0.0016 (11)
O30.0344 (13)0.0525 (19)0.0383 (13)0.0144 (12)0.0123 (11)0.0079 (12)
O40.0395 (14)0.057 (2)0.0376 (13)0.0102 (13)0.0152 (11)0.0078 (13)
O50.0302 (12)0.0501 (18)0.0375 (13)0.0084 (12)0.0001 (10)0.0151 (12)
C10.0282 (16)0.033 (2)0.0300 (17)0.0029 (16)0.0078 (14)0.0004 (15)
C20.0288 (17)0.041 (3)0.0337 (18)0.0067 (16)0.0046 (14)0.0063 (16)
C30.0314 (18)0.048 (3)0.0403 (19)0.0028 (17)0.0050 (15)0.0116 (17)
C40.0247 (16)0.040 (2)0.0306 (17)0.0003 (16)0.0036 (14)0.0073 (16)
N110.0262 (13)0.0342 (19)0.0291 (14)0.0054 (13)0.0066 (11)0.0020 (12)
N210.0293 (14)0.0323 (19)0.0363 (15)0.0040 (13)0.0065 (12)0.0006 (13)
C120.0280 (16)0.036 (2)0.0311 (17)0.0005 (16)0.0120 (14)0.0005 (15)
C130.0274 (16)0.039 (2)0.0284 (17)0.0034 (15)0.0099 (13)0.0046 (15)
C140.0236 (15)0.027 (2)0.0291 (16)0.0002 (14)0.0062 (13)0.0013 (14)
C150.0383 (19)0.049 (3)0.0279 (17)0.0137 (18)0.0113 (15)0.0000 (16)
C160.043 (2)0.052 (3)0.0243 (16)0.0145 (19)0.0100 (15)0.0034 (16)
C220.0319 (18)0.045 (3)0.0335 (18)0.0094 (17)0.0133 (15)0.0016 (17)
C230.0319 (17)0.042 (3)0.0315 (17)0.0061 (16)0.0085 (14)0.0031 (16)
C240.0254 (15)0.027 (2)0.0287 (16)0.0017 (14)0.0056 (13)0.0044 (14)
C250.0294 (17)0.037 (2)0.0296 (17)0.0029 (16)0.0080 (13)0.0010 (15)
C260.0317 (17)0.031 (2)0.0328 (17)0.0015 (16)0.0055 (14)0.0023 (15)
Geometric parameters (Å, º) top
O1—C11.304 (4)N21—C261.341 (4)
O1—H10.84C12—C131.387 (5)
O2—C11.219 (4)C12—H120.95
O3—C41.311 (4)C13—C141.384 (4)
O3—H30.84C13—H130.95
O4—C41.206 (4)C14—C151.392 (4)
O5—C21.410 (4)C14—C241.499 (4)
O5—H50.84C15—C161.384 (5)
C1—C21.524 (5)C15—H150.95
C2—C31.525 (5)C16—H160.95
C2—H21.00C22—C231.390 (5)
C3—C41.514 (5)C22—H220.95
C3—H3A0.99C23—C241.398 (4)
C3—H3B0.99C23—H230.95
N11—C121.324 (4)C24—C251.389 (4)
N11—C161.331 (4)C25—C261.388 (4)
N11—H110.88C25—H250.95
N21—C221.327 (4)C26—H260.95
C1—O1—H1109.5C14—C13—C12119.4 (3)
C4—O3—H3109.5C14—C13—H13120.3
C2—O5—H5109.5C12—C13—H13120.3
O2—C1—O1125.3 (3)C13—C14—C15117.5 (3)
O2—C1—C2121.3 (3)C13—C14—C24120.9 (3)
O1—C1—C2113.4 (3)C15—C14—C24121.7 (3)
O5—C2—C1112.7 (3)C16—C15—C14119.9 (3)
O5—C2—C3108.2 (3)C16—C15—H15120.1
C1—C2—C3109.8 (3)C14—C15—H15120.1
O5—C2—H2108.7N11—C16—C15121.6 (3)
C1—C2—H2108.7N11—C16—H16119.2
C3—C2—H2108.7C15—C16—H16119.2
C4—C3—C2111.1 (3)N21—C22—C23123.6 (3)
C4—C3—H3A109.4N21—C22—H22118.2
C2—C3—H3A109.4C23—C22—H22118.2
C4—C3—H3B109.4C22—C23—C24118.8 (3)
C2—C3—H3B109.4C22—C23—H23120.6
H3A—C3—H3B108.0C24—C23—H23120.6
O4—C4—O3123.9 (3)C25—C24—C23117.9 (3)
O4—C4—C3123.4 (3)C25—C24—C14120.7 (3)
O3—C4—C3112.7 (3)C23—C24—C14121.5 (3)
C12—N11—C16119.4 (3)C26—C25—C24118.9 (3)
C12—N11—H11120.3C26—C25—H25120.6
C16—N11—H11120.3C24—C25—H25120.6
C22—N21—C26117.3 (3)N21—C26—C25123.5 (3)
N11—C12—C13122.3 (3)N21—C26—H26118.2
N11—C12—H12118.9C25—C26—H26118.2
C13—C12—H12118.9
O2—C1—C2—O55.0 (5)C12—N11—C16—C150.0 (5)
O1—C1—C2—O5173.3 (3)C14—C15—C16—N110.4 (6)
O2—C1—C2—C3115.7 (3)C26—N21—C22—C230.9 (5)
O1—C1—C2—C366.0 (4)N21—C22—C23—C240.2 (5)
O5—C2—C3—C460.7 (4)C22—C23—C24—C250.4 (5)
C1—C2—C3—C4175.8 (3)C22—C23—C24—C14179.1 (3)
C2—C3—C4—O466.8 (4)C13—C14—C24—C258.2 (5)
C2—C3—C4—O3112.6 (3)C15—C14—C24—C25172.4 (3)
C16—N11—C12—C130.3 (5)C13—C14—C24—C23172.4 (3)
N11—C12—C13—C140.3 (5)C15—C14—C24—C237.0 (5)
C12—C13—C14—C150.1 (5)C23—C24—C25—C260.3 (5)
C12—C13—C14—C24179.5 (3)C14—C24—C25—C26179.2 (3)
C13—C14—C15—C160.4 (5)C22—N21—C26—C251.0 (5)
C24—C14—C15—C16179.8 (3)C24—C25—C26—N210.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N110.841.742.549 (3)161
O3—H3···N21i0.841.812.638 (3)171
O5—H5···O20.842.312.716 (3)110
O5—H5···O2ii0.842.082.889 (3)161
N11—H11···O10.881.672.549 (3)176
C12—H12···O2iii0.952.443.360 (4)164
C13—H13···O5iv0.952.483.302 (4)145
C16—H16···O1v0.952.393.327 (4)169
C23—H23···O4v0.952.493.434 (4)170
Symmetry codes: (i) x1, y2, z; (ii) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y+3/2, z+1/2; (v) x+1, y+1, z.
(5) 1,2-Bis-(4'-pyridyl)ethene–(S)-malic acid (1/1) top
Crystal data top
C12H11N2·C4H5O5Z = 1
Mr = 316.31F(000) = 166
Triclinic, P1Dx = 1.453 Mg m3
a = 4.9325 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3343 (4) ÅCell parameters from 1174 reflections
c = 9.3502 (7) Åθ = 4.2–25.2°
α = 72.751 (2)°µ = 0.11 mm1
β = 89.414 (2)°T = 150 K
γ = 80.207 (2)°Plate, colourless
V = 361.41 (4) Å30.32 × 0.30 × 0.18 mm
Data collection top
Kappa-CCD
diffractometer
2167 independent reflections
Radiation source: fine-focus sealed X-ray tube1958 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ scans, and ω scans with κ offsetsθmax = 25.2°, θmin = 4.2°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 55
Tmin = 0.966, Tmax = 0.981k = 99
3171 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0558P)2 + 0.1P]
where P = (Fo2 + 2Fc2)/3
2167 reflections(Δ/σ)max = 0.004
179 parametersΔρmax = 0.31 e Å3
65 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1770 (5)0.4736 (3)0.7433 (3)0.0391 (6)
O20.1626 (5)0.7361 (3)0.5892 (3)0.0386 (6)
O30.8240 (6)0.5326 (3)0.2644 (3)0.0493 (7)
O40.8080 (5)0.2620 (3)0.3901 (3)0.0416 (6)
O50.7073 (5)0.3826 (3)0.6727 (3)0.0384 (5)
C10.2724 (7)0.5798 (4)0.6424 (4)0.0309 (7)
C20.5393 (7)0.5249 (4)0.5705 (4)0.0316 (8)
C30.4595 (7)0.4750 (5)0.4331 (4)0.0392 (9)
C40.7154 (7)0.4256 (5)0.3529 (4)0.0351 (8)
N211.7570 (4)1.1735 (2)1.2546 (2)0.0301 (6)*0.529 (4)
C221.7068 (12)1.2875 (6)1.1272 (5)0.0321 (9)*0.529 (4)
C231.4878 (10)1.2531 (6)1.0398 (5)0.0289 (10)*0.529 (4)
C241.3134 (9)1.0955 (6)1.0842 (5)0.0222 (9)*0.529 (4)
C251.3716 (11)0.9785 (6)1.2166 (5)0.0286 (9)*0.529 (4)
C261.5886 (13)1.0229 (5)1.3016 (7)0.0305 (9)*0.529 (4)
C271.0854 (10)1.0612 (7)0.9918 (6)0.0285 (13)*0.529 (4)
N110.2485 (4)0.8209 (2)0.7372 (2)0.0283 (6)*0.529 (4)
C120.3010 (12)0.7007 (5)0.8597 (5)0.0315 (8)*0.529 (4)
C130.5164 (10)0.7255 (6)0.9524 (6)0.0294 (10)*0.529 (4)
C140.6835 (10)0.8855 (6)0.9159 (5)0.0242 (10)*0.529 (4)
C150.6199 (10)1.0109 (6)0.7908 (5)0.0284 (10)*0.529 (4)
C160.4010 (14)0.9770 (5)0.7029 (8)0.0323 (9)*0.529 (4)
C170.9085 (10)0.9154 (7)1.0119 (6)0.0242 (12)*0.529 (4)
N21A1.7570 (4)1.1735 (2)1.2546 (2)0.0301 (6)*0.471 (4)
C22A1.6700 (13)1.2600 (7)1.1230 (5)0.0321 (9)*0.471 (4)
C23A1.4447 (11)1.1941 (6)1.0542 (6)0.0289 (10)*0.471 (4)
C24A1.2970 (10)1.0321 (6)1.1249 (6)0.0222 (9)*0.471 (4)
C25A1.3921 (11)0.9407 (7)1.2601 (6)0.0286 (9)*0.471 (4)
C26A1.6298 (14)1.0126 (5)1.3155 (8)0.0305 (9)*0.471 (4)
C27A1.0623 (11)0.9507 (7)1.0616 (6)0.0255 (14)*0.471 (4)
N11A0.2485 (4)0.8209 (2)0.7372 (2)0.0283 (6)*0.471 (4)
C12A0.3400 (13)0.7184 (6)0.8596 (6)0.0315 (8)*0.471 (4)
C13A0.5672 (11)0.7811 (7)0.9290 (6)0.0294 (10)*0.471 (4)
C14A0.6998 (11)0.9497 (6)0.8719 (6)0.0242 (10)*0.471 (4)
C15A0.6001 (11)1.0537 (7)0.7442 (6)0.0284 (10)*0.471 (4)
C16A0.3749 (16)0.9825 (5)0.6789 (8)0.0323 (9)*0.471 (4)
C17A0.9387 (12)1.0228 (8)0.9389 (7)0.0303 (15)*0.471 (4)
H40.94640.24320.34060.062*
H50.84810.41300.69880.058*
H20.64260.62220.53820.038*
H3A0.35930.37780.46530.047*
H3B0.33570.57230.36350.047*
H221.82451.39541.09540.039*0.529 (4)
H231.45731.33700.94990.035*0.529 (4)
H251.26250.86771.24910.034*0.529 (4)
H261.61760.94441.39510.037*0.529 (4)
H271.05911.15320.90720.034*0.529 (4)
H110.07540.79320.66290.034*
H120.18480.59220.88490.038*0.529 (4)
H130.54830.63611.03780.035*0.529 (4)
H150.72841.12190.76480.034*0.529 (4)
H160.35991.06480.61860.039*0.529 (4)
H170.93160.82271.09660.029*0.529 (4)
H22A1.76651.37161.07410.039*0.471 (4)
H23A1.39221.25930.95960.035*0.471 (4)
H25A1.29590.83071.31380.034*0.471 (4)
H26A1.70550.94381.40110.037*0.471 (4)
H27A0.99080.83471.11310.031*0.471 (4)
H12A0.25030.60320.89910.038*0.471 (4)
H13A0.63240.70821.01600.035*0.471 (4)
H15A0.68361.16990.70280.034*0.471 (4)
H16A0.30861.05120.58990.039*0.471 (4)
H17A1.01631.13790.88760.036*0.471 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0288 (13)0.0401 (13)0.0477 (14)0.0031 (10)0.0083 (11)0.0138 (11)
O20.0332 (13)0.0364 (13)0.0435 (13)0.0015 (10)0.0135 (10)0.0125 (10)
O30.0509 (17)0.0432 (15)0.0509 (15)0.0031 (12)0.0160 (13)0.0165 (12)
O40.0365 (14)0.0431 (14)0.0511 (15)0.0052 (10)0.0225 (11)0.0248 (11)
O50.0290 (12)0.0400 (11)0.0464 (12)0.0013 (8)0.0047 (9)0.0159 (9)
C10.0288 (17)0.0358 (18)0.0334 (17)0.0079 (14)0.0056 (14)0.0173 (14)
C20.0304 (19)0.0326 (16)0.0334 (16)0.0001 (13)0.0022 (14)0.0155 (13)
C30.0243 (18)0.055 (2)0.046 (2)0.0019 (15)0.0038 (15)0.0312 (17)
C40.0319 (19)0.0413 (19)0.0356 (18)0.0016 (15)0.0001 (15)0.0212 (16)
Geometric parameters (Å, º) top
O1—C11.238 (4)C12—H120.95
O2—C11.272 (4)C13—C141.392 (2)
O3—C41.218 (4)C13—H130.95
O4—C41.303 (4)C14—C151.392 (2)
O4—H40.84C14—C171.455 (5)
O5—C21.421 (4)C15—C161.392 (2)
O5—H50.84C15—H150.95
C1—C21.534 (4)C16—H160.95
C2—C31.537 (4)C17—H170.95
C2—H21.00C22A—C23A1.392 (2)
C3—C41.520 (5)C22A—H22A0.95
C3—H3A0.99C23A—C24A1.392 (2)
C3—H3B0.99C23A—H23A0.95
N21—C221.336 (2)C24A—C25A1.392 (2)
N21—C261.336 (2)C24A—C27A1.452 (5)
C22—C231.391 (2)C25A—C26A1.391 (2)
C22—H220.95C25A—H25A0.95
C23—C241.392 (2)C26A—H26A0.95
C23—H230.95C27A—C17A1.323 (6)
C24—C251.392 (2)C27A—H27A0.95
C24—C271.453 (5)C12A—C13A1.392 (2)
C25—C261.392 (2)C12A—H12A0.95
C25—H250.95C13A—C14A1.392 (2)
C26—H260.95C13A—H13A0.95
C27—C171.334 (5)C14A—C15A1.392 (2)
C27—H270.95C14A—C17A1.456 (6)
N11—C121.336 (2)C15A—C16A1.392 (2)
N11—C161.336 (2)C15A—H15A0.95
N11—H111.1317C16A—H16A0.95
C12—C131.391 (2)C17A—H17A0.95
C1—O2—H11116.2C13—C12—H12118.1
C4—O4—H4109.5C12—C13—C14117.8 (5)
C2—O5—H5109.5C12—C13—H13121.1
O1—C1—O2124.8 (3)C14—C13—H13121.1
O1—C1—C2119.9 (3)C13—C14—C15117.6 (4)
O2—C1—C2115.3 (3)C13—C14—C17119.0 (4)
O5—C2—C1110.8 (3)C15—C14—C17123.4 (4)
O5—C2—C3109.3 (2)C16—C15—C14121.4 (5)
C1—C2—C3107.7 (2)C16—C15—H15119.3
O5—C2—H2109.7C14—C15—H15119.3
C1—C2—H2109.7N11—C16—C15119.9 (4)
C3—C2—H2109.7N11—C16—H16120.0
C4—C3—C2110.3 (2)C15—C16—H16120.0
C4—C3—H3A109.6C27—C17—C14125.9 (4)
C2—C3—H3A109.6C27—C17—H17117.0
C4—C3—H3B109.6C14—C17—H17117.0
C2—C3—H3B109.6C23A—C22A—H22A118.5
H3A—C3—H3B108.1C24A—C23A—C22A119.5 (5)
O3—C4—O4124.1 (3)C24A—C23A—H23A120.2
O3—C4—C3121.6 (3)C22A—C23A—H23A120.2
O4—C4—C3114.3 (3)C23A—C24A—C25A117.2 (5)
C22—N21—C26119.2 (3)C23A—C24A—C27A123.9 (4)
N21—C22—C23122.1 (4)C25A—C24A—C27A118.8 (4)
N21—C22—H22118.9C26A—C25A—C24A119.2 (5)
C23—C22—H22118.9C26A—C25A—H25A120.4
C22—C23—C24119.9 (4)C24A—C25A—H25A120.4
C22—C23—H23120.1C25A—C26A—H26A118.3
C24—C23—H23120.1C17A—C27A—C24A126.1 (5)
C23—C24—C25116.9 (4)C17A—C27A—H27A116.9
C23—C24—C27119.3 (4)C24A—C27A—H27A116.9
C25—C24—C27123.8 (4)C13A—C12A—H12A120.1
C26—C25—C24120.4 (5)C14A—C13A—C12A120.5 (5)
C26—C25—H25119.8C14A—C13A—H13A119.7
C24—C25—H25119.8C12A—C13A—H13A119.7
N21—C26—C25121.4 (4)C13A—C14A—C15A118.6 (5)
N21—C26—H26119.3C13A—C14A—C17A123.2 (4)
C25—C26—H26119.3C15A—C14A—C17A118.2 (4)
C17—C27—C24127.5 (4)C16A—C15A—C14A118.1 (5)
C17—C27—H27116.2C16A—C15A—H15A121.0
C24—C27—H27116.2C14A—C15A—H15A121.0
C12—N11—C16119.4 (3)C15A—C16A—H16A118.9
C12—N11—H11121.1C27A—C17A—C14A128.8 (5)
C16—N11—H11119.5C27A—C17A—H17A115.6
N11—C12—C13123.7 (4)C14A—C17A—H17A115.6
N11—C12—H12118.1
O1—C1—C2—O527.5 (4)C12—C13—C14—C17179.4 (5)
O2—C1—C2—O5153.6 (3)C13—C14—C15—C161.4 (10)
O1—C1—C2—C392.0 (3)C17—C14—C15—C16179.4 (7)
O2—C1—C2—C386.9 (3)C12—N11—C16—C152.9 (11)
O5—C2—C3—C461.7 (3)C14—C15—C16—N110.7 (12)
C1—C2—C3—C4177.9 (3)C24—C27—C17—C14179.4 (7)
C2—C3—C4—O382.4 (4)C13—C14—C17—C27180.0 (5)
C2—C3—C4—O496.2 (3)C15—C14—C17—C272.0 (8)
C26—N21—C22—C231.5 (8)C22A—C23A—C24A—C25A2.7 (9)
N21—C22—C23—C240.2 (8)C22A—C23A—C24A—C27A178.9 (6)
C22—C23—C24—C250.4 (8)C23A—C24A—C25A—C26A1.5 (10)
C22—C23—C24—C27180.0 (5)C27A—C24A—C25A—C26A174.9 (7)
C23—C24—C25—C262.5 (9)C23A—C24A—C27A—C17A7.7 (10)
C27—C24—C25—C26177.8 (7)C25A—C24A—C27A—C17A176.2 (6)
C22—N21—C26—C253.7 (11)C12A—C13A—C14A—C15A0.0 (9)
C24—C25—C26—N214.3 (12)C12A—C13A—C14A—C17A179.8 (6)
C23—C24—C27—C17175.8 (5)C13A—C14A—C15A—C16A0.9 (10)
C25—C24—C27—C173.8 (9)C17A—C14A—C15A—C16A178.9 (8)
C16—N11—C12—C133.0 (9)C24A—C27A—C17A—C14A178.4 (8)
N11—C12—C13—C140.9 (9)C13A—C14A—C17A—C27A2.5 (10)
C12—C13—C14—C151.3 (8)C15A—C14A—C17A—C27A177.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N21i0.841.762.591 (3)172
O5—H5···O1ii0.841.862.702 (3)175
N11—H11···O21.131.442.561 (3)171
C16—H16···O4iii0.952.513.451 (7)171
C23—H23···O1iv0.952.523.136 (5)123
C26—H26···O2v0.952.493.401 (7)160
C27—H27···O5iv0.952.573.393 (6)145
Symmetry codes: (i) x+3, y1, z1; (ii) x+1, y, z; (iii) x1, y+1, z; (iv) x2, y+1, z; (v) x2, y, z+1.
(6) 1,2-Bis-(4'-pyridyl)ethene–racemic malic acid (1/1) top
Crystal data top
2(C6H5N)·C4H6O5Z = 1
Mr = 316.31F(000) = 166
Triclinic, P1Dx = 1.446 Mg m3
a = 4.9566 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4178 (10) ÅCell parameters from 1243 reflections
c = 9.2538 (14) Åθ = 2.9–25.1°
α = 73.213 (5)°µ = 0.11 mm1
β = 89.915 (6)°T = 150 K
γ = 79.750 (7)°Plate, colourless
V = 363.24 (8) Å30.30 × 0.30 × 0.12 mm
Data collection top
Kappa-CCD
diffractometer
1286 independent reflections
Radiation source: fine-focus sealed X-ray tube774 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
φ scans, and ω scans with κ offsetsθmax = 25.1°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 50
Tmin = 0.968, Tmax = 0.987k = 109
3458 measured reflectionsl = 1011
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0867P)2]
where P = (Fo2 + 2Fc2)/3
1286 reflections(Δ/σ)max < 0.001
131 parametersΔρmax = 0.23 e Å3
32 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1686 (4)0.7374 (2)0.5969 (2)0.0597 (7)
O20.1810 (4)0.4751 (2)0.7389 (3)0.0821 (8)
O50.7175 (7)0.3878 (4)0.6921 (4)0.0564 (10)0.50
C10.2780 (6)0.5790 (4)0.6433 (4)0.0604 (8)
C20.5392 (6)0.5282 (4)0.5671 (4)0.0692 (9)
N110.2457 (3)0.82431 (19)0.74047 (18)0.0423 (6)0.50
C120.3349 (11)0.7343 (7)0.8692 (5)0.0444 (10)0.50
C130.5620 (11)0.7980 (6)0.9377 (8)0.0413 (14)0.50
C140.7036 (10)0.9616 (5)0.8708 (5)0.0328 (13)0.50
C150.6078 (14)1.0535 (8)0.7368 (6)0.0404 (14)0.50
C160.3791 (13)0.9816 (4)0.6747 (7)0.0458 (10)0.50
C170.9429 (9)1.0353 (6)0.9373 (4)0.0464 (10)0.50
N210.2457 (3)0.82431 (19)0.74047 (18)0.0423 (6)0.50
C220.2976 (12)0.7054 (7)0.8627 (5)0.0444 (10)0.50
C230.5139 (12)0.7362 (6)0.9528 (8)0.0413 (14)0.50
C240.6839 (10)0.8943 (5)0.9170 (5)0.0328 (13)0.50
C250.6260 (14)1.0163 (8)0.7892 (6)0.0404 (14)0.50
C260.4062 (12)0.9770 (4)0.7040 (7)0.0458 (10)0.50
C270.9114 (8)0.9277 (5)1.0110 (6)0.0464 (10)0.50
H10.044 (6)0.7650 (11)0.671 (3)0.090*
H50.915 (12)0.432 (4)0.717 (5)0.085*0.50
H2A0.63490.62650.53150.083*
H2B0.65490.43600.64840.084*0.50
H120.23960.62250.91570.053*0.50
H130.61980.73051.02930.050*0.50
H150.69881.16570.68760.048*0.50
H160.31621.04600.58310.055*0.50
H171.02131.14400.88270.056*0.50
H220.18370.59670.88880.053*0.50
H230.54580.64911.03910.050*0.50
H250.73621.12610.76020.048*0.50
H260.36911.06160.61710.055*0.50
H270.92920.83871.09310.056*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0597 (13)0.0554 (12)0.0605 (13)0.0025 (9)0.0227 (10)0.0197 (9)
O20.0610 (15)0.0556 (13)0.115 (2)0.0012 (11)0.0157 (13)0.0101 (13)
O50.053 (2)0.047 (2)0.060 (2)0.0020 (17)0.0008 (18)0.0091 (17)
C10.0547 (19)0.0573 (18)0.069 (2)0.0027 (15)0.0036 (15)0.0258 (15)
C20.0519 (18)0.070 (2)0.092 (2)0.0025 (15)0.0033 (16)0.0402 (17)
N110.0418 (13)0.0432 (12)0.0426 (13)0.0030 (9)0.0082 (10)0.0164 (10)
C120.042 (2)0.044 (2)0.0486 (17)0.0012 (16)0.0120 (13)0.0213 (15)
C130.041 (3)0.036 (5)0.046 (2)0.001 (3)0.011 (2)0.015 (3)
C140.0357 (18)0.025 (4)0.032 (3)0.003 (2)0.003 (2)0.005 (3)
C150.0451 (19)0.041 (3)0.029 (4)0.000 (2)0.012 (3)0.006 (3)
C160.0496 (19)0.0488 (16)0.039 (2)0.0007 (13)0.0132 (17)0.0189 (14)
C170.046 (3)0.047 (3)0.047 (3)0.005 (3)0.004 (2)0.0159 (18)
N210.0418 (13)0.0432 (12)0.0426 (13)0.0030 (9)0.0082 (10)0.0164 (10)
C220.042 (2)0.044 (2)0.0486 (17)0.0012 (16)0.0120 (13)0.0213 (15)
C230.041 (3)0.036 (5)0.046 (2)0.001 (3)0.011 (2)0.015 (3)
C240.0357 (18)0.025 (4)0.032 (3)0.003 (2)0.003 (2)0.005 (3)
C250.0451 (19)0.041 (3)0.029 (4)0.000 (2)0.012 (3)0.006 (3)
C260.0496 (19)0.0488 (16)0.039 (2)0.0007 (13)0.0132 (17)0.0189 (14)
C270.046 (3)0.047 (3)0.047 (3)0.005 (3)0.004 (2)0.0159 (18)
Geometric parameters (Å, º) top
O1—C11.292 (3)C14—C171.458 (6)
O1—H11.2772C15—C161.392 (2)
O2—C11.217 (4)C15—H150.95
O5—C21.536 (5)C16—H160.95
O5—H51.15C17—H170.92
C1—C21.527 (4)C22—C231.392 (2)
C2—C2i1.525 (6)C22—H220.95
C2—H2A1.00C23—C241.392 (2)
C2—H2B1.001 (3)C23—H230.95
N11—C121.336 (2)C24—C251.392 (2)
N11—C161.336 (2)C24—C271.461 (6)
C12—C131.392 (2)C25—C261.392 (2)
C12—H120.95C25—H250.95
C13—C141.392 (2)C26—H260.95
C13—H130.95C27—H270.92
C14—C151.392 (2)
C1—O1—H1109.5C13—C14—C15117.3 (6)
C2—O5—H5109.5C13—C14—C17121.9 (4)
H5—O5—H2B110.1C15—C14—C17120.8 (4)
O2—C1—O1123.4 (3)C16—C15—C14120.2 (6)
O2—C1—C2121.3 (3)C16—C15—H15119.9
O1—C1—C2115.2 (3)C14—C15—H15119.9
C1—C2—C2i108.6 (3)N11—C16—C15121.7 (5)
C1—C2—O5104.7 (3)N11—C16—H16119.2
C2i—C2—O5113.9 (3)C15—C16—H16119.2
C1—C2—H2A109.8C14—C17—H17114.4
C2i—C2—H2A109.8C23—C22—H22119.1
O5—C2—H2A109.8C22—C23—C24120.2 (6)
C1—C2—H2B104.7 (3)C22—C23—H23119.9
C2i—C2—H2B113.5 (3)C24—C23—H23119.9
H2A—C2—H2B110.2C25—C24—C23117.0 (6)
C12—N11—C16118.9 (4)C25—C24—C27122.5 (4)
N11—C12—C13122.5 (5)C23—C24—C27120.5 (4)
N11—C12—H12118.7C24—C25—C26119.8 (6)
C13—C12—H12118.7C24—C25—H25120.1
C12—C13—C14119.4 (6)C26—C25—H25120.1
C12—C13—H13120.3C25—C26—H26118.9
C14—C13—H13120.3C24—C27—H27115.1
O2—C1—C2—C2i86.0 (4)C13—C14—C15—C160.00 (9)
O1—C1—C2—C2i92.9 (4)C17—C14—C15—C16179.98 (6)
O2—C1—C2—O536.0 (4)C12—N11—C16—C150.03 (7)
O1—C1—C2—O5145.1 (3)C14—C15—C16—N110.03 (10)
C16—N11—C12—C130.02 (3)C22—C23—C24—C250.01 (7)
N11—C12—C13—C140.01 (3)C22—C23—C24—C27180.00 (4)
C12—C13—C14—C150.01 (7)C23—C24—C25—C260.00 (9)
C12—C13—C14—C17180.00 (4)C27—C24—C25—C26179.98 (6)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N111.281.292.556 (2)168
O5—H5···O2ii1.151.462.606 (4)173
C16—H16···O1iii0.952.313.231 (6)162
C17—H17···O5iv0.922.443.336 (6)163
Symmetry codes: (ii) x+1, y, z; (iii) x, y+2, z+1; (iv) x2, y+1, z.
(7) 1,4-Diazabicyclo[2.2.2]octane–racemic malic acid (1/2) top
Crystal data top
C6H14N2·2(C4H5O5)F(000) = 1616
Mr = 380.35Dx = 1.520 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.7309 (3) ÅCell parameters from 7524 reflections
b = 20.9103 (5) Åθ = 2.6–27.5°
c = 12.5400 (3) ŵ = 0.13 mm1
β = 95.1780 (13)°T = 150 K
V = 3324.61 (14) Å3Block, colourless
Z = 80.32 × 0.28 × 0.25 mm
Data collection top
Kappa-CCD
diffractometer
7603 independent reflections
Radiation source: fine-focus sealed X-ray tube4395 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 1616
Tmin = 0.960, Tmax = 0.968k = 270
27049 measured reflectionsl = 016
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0827P)2]
where P = (Fo2 + 2Fc2)/3
7603 reflections(Δ/σ)max < 0.001
477 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.41 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O310.19566 (12)0.08235 (7)0.95529 (14)0.0298 (4)
O320.34918 (11)0.08840 (7)1.02664 (13)0.0261 (4)
O330.34121 (14)0.02652 (7)0.75445 (14)0.0366 (4)
O340.38660 (13)0.07572 (7)0.72874 (14)0.0316 (4)
O350.19734 (11)0.04261 (7)0.94739 (13)0.0255 (4)
C310.27671 (16)0.05708 (10)0.98577 (18)0.0226 (5)
C320.29190 (16)0.01511 (10)0.97878 (18)0.0217 (5)
C330.38806 (17)0.03469 (10)0.90436 (19)0.0252 (5)
C340.36908 (16)0.02398 (11)0.78921 (19)0.0241 (5)
O410.72979 (12)0.33317 (7)0.06519 (14)0.0314 (4)
O420.87632 (12)0.33440 (7)0.01937 (13)0.0265 (4)
O430.89313 (15)0.27364 (8)0.25743 (15)0.0398 (5)
O440.89804 (14)0.16783 (7)0.27401 (14)0.0344 (4)
O450.71985 (11)0.20890 (7)0.07055 (14)0.0275 (4)
C410.80484 (17)0.30533 (10)0.02710 (18)0.0225 (5)
C420.81313 (16)0.23303 (9)0.03164 (19)0.0214 (5)
C430.91113 (16)0.20987 (10)0.10115 (19)0.0251 (5)
C440.90077 (16)0.22107 (10)0.21825 (19)0.0242 (5)
O510.22332 (12)0.08133 (7)0.57270 (13)0.0295 (4)
O520.36071 (11)0.07624 (7)0.47544 (13)0.0249 (4)
O530.36421 (16)0.01013 (8)0.74928 (15)0.0465 (5)
O540.36728 (14)0.09545 (7)0.76492 (14)0.0331 (4)
O550.18690 (11)0.04218 (7)0.55724 (13)0.0260 (4)
C510.28875 (16)0.05042 (10)0.52499 (18)0.0213 (5)
C520.28488 (16)0.02247 (10)0.52250 (18)0.0216 (5)
C530.37806 (17)0.05265 (10)0.59126 (19)0.0251 (5)
C540.36995 (16)0.04155 (10)0.70902 (19)0.0243 (5)
O610.32047 (12)0.32925 (7)0.45456 (14)0.0299 (4)
O620.16959 (12)0.32980 (7)0.53256 (13)0.0248 (4)
O630.18862 (15)0.26389 (7)0.26083 (14)0.0362 (4)
O640.14163 (14)0.16205 (7)0.23741 (14)0.0344 (4)
O650.33439 (11)0.20396 (7)0.45648 (13)0.0240 (4)
C610.24380 (16)0.30124 (10)0.49017 (17)0.0207 (5)
C620.23717 (16)0.22826 (9)0.48722 (18)0.0204 (5)
C630.14380 (16)0.20343 (10)0.41326 (18)0.0238 (5)
C640.16017 (16)0.21353 (10)0.29713 (19)0.0226 (5)
N110.05889 (13)0.04254 (8)0.82428 (15)0.0235 (4)
N120.08793 (14)0.04396 (8)0.70412 (16)0.0237 (4)
C110.0026 (2)0.01766 (10)0.8382 (2)0.0356 (6)
C120.0948 (2)0.01470 (12)0.7702 (3)0.0529 (9)
C130.10353 (18)0.04907 (15)0.7111 (2)0.0418 (7)
C140.0135 (2)0.04582 (18)0.6389 (2)0.0654 (10)
C150.01182 (18)0.09788 (10)0.8529 (2)0.0310 (6)
C160.0974 (2)0.09986 (14)0.7765 (3)0.0588 (10)
N210.44278 (14)0.28942 (8)0.30983 (16)0.0242 (4)
N220.58228 (13)0.29243 (8)0.18237 (15)0.0231 (4)
C210.4336 (2)0.23159 (12)0.2413 (2)0.0383 (7)
C220.5134 (2)0.23524 (10)0.1594 (2)0.0335 (6)
C230.54843 (18)0.29019 (13)0.3709 (2)0.0379 (6)
C240.63326 (18)0.28926 (15)0.2931 (2)0.0422 (7)
C250.4282 (2)0.34721 (12)0.2421 (2)0.0420 (7)
C260.51628 (18)0.35108 (10)0.1681 (2)0.0327 (6)
H340.37290.06760.66590.047*
H350.20090.08260.95180.038*
H320.30240.03111.05220.026*
H33A0.40370.08040.91560.030*
H33B0.45000.00940.92180.030*
H440.88920.17670.33790.052*
H450.71210.17030.05290.041*
H420.81720.21670.04280.026*
H43A0.92140.16360.08870.030*
H43B0.97400.23280.08000.030*
H540.36370.08670.82990.050*
H550.17780.08130.54420.039*
H520.28790.03680.44680.026*
H53A0.37960.09920.57720.030*
H53B0.44490.03410.57070.030*
H640.14870.17100.17320.052*
H650.33420.16390.46050.036*
H620.22850.21290.56140.025*
H63A0.13420.15720.42650.029*
H63B0.07880.22580.43000.029*
H110.11350.04200.86880.028*
H120.14260.04450.65970.028*
H11A0.04300.05460.81630.043*
H11B0.02860.02320.91450.043*
H12A0.16180.01480.81690.064*
H12B0.09410.05280.72320.064*
H13A0.14100.09040.70090.050*
H13B0.15460.01420.69270.050*
H14A0.02120.00710.59350.079*
H14B0.01600.08370.59130.079*
H15A0.04390.09330.92750.037*
H15B0.02920.13810.84780.037*
H16A0.09100.13970.73390.071*
H16B0.16750.09960.81770.071*
H210.39100.28830.35760.029*
H220.63400.29340.13450.028*
H21A0.36150.22880.20460.046*
H21B0.44640.19290.28590.046*
H22A0.55690.19590.16260.040*
H22B0.47660.23870.08660.040*
H23A0.55620.25240.41850.045*
H23B0.55590.32910.41590.045*
H24A0.68120.32620.30690.051*
H24B0.67540.24960.30280.051*
H25A0.42930.38580.28790.050*
H25B0.35910.34530.19920.050*
H26A0.48600.35450.09280.039*
H26B0.56010.38950.18550.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.0305 (9)0.0229 (8)0.0376 (11)0.0061 (7)0.0127 (7)0.0043 (7)
O320.0283 (8)0.0245 (8)0.0264 (10)0.0043 (7)0.0080 (7)0.0000 (7)
O330.0533 (11)0.0291 (9)0.0273 (11)0.0086 (8)0.0032 (8)0.0045 (8)
O340.0433 (10)0.0309 (9)0.0216 (10)0.0055 (7)0.0086 (8)0.0014 (7)
O350.0238 (8)0.0195 (8)0.0341 (11)0.0020 (6)0.0084 (7)0.0021 (7)
C310.0256 (11)0.0249 (11)0.0174 (13)0.0005 (9)0.0027 (9)0.0004 (9)
C320.0235 (11)0.0233 (11)0.0188 (13)0.0015 (9)0.0046 (9)0.0006 (9)
C330.0255 (11)0.0264 (12)0.0240 (14)0.0034 (9)0.0029 (9)0.0004 (10)
C340.0199 (11)0.0274 (12)0.0250 (14)0.0001 (9)0.0009 (9)0.0002 (10)
O410.0339 (9)0.0236 (8)0.0395 (11)0.0075 (7)0.0180 (8)0.0065 (7)
O420.0291 (8)0.0253 (8)0.0263 (10)0.0008 (7)0.0091 (7)0.0019 (7)
O430.0608 (12)0.0301 (9)0.0280 (11)0.0020 (8)0.0018 (9)0.0039 (8)
O440.0515 (11)0.0281 (9)0.0253 (10)0.0041 (8)0.0137 (9)0.0024 (7)
O450.0240 (8)0.0235 (8)0.0362 (11)0.0027 (6)0.0091 (7)0.0039 (7)
C410.0258 (11)0.0233 (11)0.0185 (13)0.0012 (9)0.0028 (9)0.0021 (9)
C420.0227 (11)0.0195 (11)0.0224 (13)0.0016 (8)0.0040 (9)0.0030 (9)
C430.0237 (11)0.0269 (12)0.0254 (14)0.0036 (9)0.0057 (9)0.0006 (10)
C440.0197 (10)0.0255 (12)0.0270 (14)0.0004 (9)0.0006 (9)0.0005 (10)
O510.0359 (9)0.0213 (8)0.0336 (11)0.0048 (7)0.0158 (8)0.0017 (7)
O520.0277 (8)0.0241 (8)0.0238 (9)0.0017 (6)0.0082 (7)0.0005 (7)
O530.0883 (15)0.0233 (9)0.0267 (11)0.0016 (9)0.0004 (10)0.0018 (8)
O540.0488 (10)0.0251 (8)0.0271 (10)0.0058 (7)0.0131 (8)0.0042 (7)
O550.0243 (8)0.0238 (8)0.0306 (10)0.0017 (6)0.0070 (7)0.0039 (7)
C510.0220 (10)0.0243 (11)0.0176 (12)0.0001 (9)0.0010 (9)0.0013 (9)
C520.0215 (11)0.0249 (11)0.0188 (13)0.0001 (9)0.0042 (9)0.0000 (9)
C530.0251 (11)0.0237 (11)0.0268 (14)0.0037 (9)0.0035 (9)0.0016 (10)
C540.0225 (11)0.0263 (12)0.0235 (13)0.0028 (9)0.0007 (9)0.0044 (10)
O610.0338 (9)0.0233 (8)0.0347 (11)0.0064 (7)0.0141 (7)0.0042 (7)
O620.0280 (8)0.0233 (8)0.0239 (9)0.0035 (6)0.0069 (7)0.0018 (7)
O630.0583 (12)0.0257 (9)0.0247 (10)0.0031 (8)0.0043 (8)0.0022 (7)
O640.0482 (10)0.0314 (9)0.0252 (10)0.0143 (8)0.0114 (8)0.0086 (8)
O650.0246 (8)0.0194 (8)0.0286 (10)0.0018 (6)0.0054 (6)0.0005 (7)
C610.0236 (11)0.0232 (11)0.0153 (12)0.0012 (9)0.0013 (9)0.0006 (9)
C620.0235 (11)0.0217 (11)0.0168 (12)0.0011 (9)0.0055 (9)0.0009 (9)
C630.0247 (11)0.0259 (11)0.0214 (13)0.0044 (9)0.0051 (9)0.0030 (9)
C640.0187 (10)0.0237 (11)0.0253 (14)0.0008 (9)0.0013 (9)0.0012 (10)
N110.0200 (9)0.0272 (10)0.0242 (12)0.0009 (7)0.0064 (8)0.0002 (8)
N120.0227 (9)0.0247 (10)0.0245 (11)0.0020 (7)0.0064 (8)0.0026 (8)
C110.0454 (15)0.0213 (12)0.0433 (18)0.0039 (11)0.0210 (12)0.0041 (11)
C120.0617 (18)0.0373 (15)0.066 (2)0.0214 (14)0.0401 (17)0.0241 (15)
C130.0246 (12)0.075 (2)0.0255 (16)0.0033 (12)0.0009 (11)0.0055 (14)
C140.0256 (14)0.141 (3)0.0294 (18)0.0136 (17)0.0007 (12)0.0091 (19)
C150.0332 (13)0.0261 (12)0.0344 (16)0.0038 (10)0.0073 (11)0.0057 (11)
C160.0609 (19)0.0481 (17)0.074 (2)0.0297 (15)0.0402 (17)0.0342 (16)
N210.0218 (9)0.0263 (10)0.0254 (12)0.0015 (8)0.0069 (8)0.0018 (8)
N220.0209 (9)0.0251 (10)0.0240 (11)0.0026 (8)0.0059 (8)0.0022 (8)
C210.0414 (14)0.0389 (14)0.0371 (17)0.0138 (12)0.0183 (12)0.0130 (12)
C220.0391 (14)0.0252 (12)0.0384 (17)0.0041 (10)0.0160 (12)0.0061 (11)
C230.0291 (13)0.0619 (18)0.0224 (15)0.0049 (12)0.0005 (10)0.0039 (12)
C240.0237 (12)0.078 (2)0.0241 (15)0.0014 (12)0.0011 (10)0.0087 (14)
C250.0411 (15)0.0338 (14)0.054 (2)0.0135 (12)0.0207 (13)0.0162 (13)
C260.0315 (12)0.0220 (11)0.0459 (17)0.0030 (10)0.0103 (11)0.0088 (11)
Geometric parameters (Å, º) top
O31—C311.249 (2)C63—C641.504 (3)
O32—C311.276 (2)C63—H63A0.99
O33—C341.208 (3)C63—H63B0.99
O34—C341.328 (3)N11—C111.484 (3)
O34—H340.84N11—C131.487 (3)
O35—C321.421 (2)N11—C151.490 (3)
O35—H350.84N11—H110.93
C31—C321.523 (3)N12—C141.465 (3)
C32—C331.527 (3)N12—C121.478 (3)
C32—H321.00N12—C161.478 (3)
C33—C341.502 (3)N12—H120.93
C33—H33A0.99C11—C121.514 (3)
C33—H33B0.99C11—H11A0.99
O41—C411.250 (3)C11—H11B0.99
O42—C411.278 (2)C12—H12A0.99
O43—C441.212 (3)C12—H12B0.99
O44—C441.317 (3)C13—C141.525 (3)
O44—H440.84C13—H13A0.99
O45—C421.417 (2)C13—H13B0.99
O45—H450.84C14—H14A0.99
C41—C421.516 (3)C14—H14B0.99
C42—C431.534 (3)C15—C161.515 (3)
C42—H421.00C15—H15A0.99
C43—C441.505 (3)C15—H15B0.99
C43—H43A0.99C16—H16A0.99
C43—H43B0.99C16—H16B0.99
O51—C511.249 (2)N21—C251.479 (3)
O52—C511.273 (2)N21—C211.482 (3)
O53—C541.198 (3)N21—C231.486 (3)
O54—C541.329 (3)N21—H210.93
O54—H540.84N22—C241.480 (3)
O55—C521.419 (2)N22—C261.488 (3)
O55—H550.84N22—C221.496 (3)
C51—C521.525 (3)N22—H220.93
C52—C531.538 (3)C21—C221.510 (3)
C52—H521.00C21—H21A0.99
C53—C541.508 (3)C21—H21B0.99
C53—H53A0.99C22—H22A0.99
C53—H53B0.99C22—H22B0.99
O61—C611.255 (2)C23—C241.519 (3)
O62—C611.274 (2)C23—H23A0.99
O63—C641.215 (3)C23—H23B0.99
O64—C641.320 (3)C24—H24A0.99
O64—H640.84C24—H24B0.99
O65—C621.423 (2)C25—C261.520 (3)
O65—H650.84C25—H25A0.99
C61—C621.529 (3)C25—H25B0.99
C62—C631.531 (3)C26—H26A0.99
C62—H621.00C26—H26B0.99
C34—O34—H34109.5C12—N12—C16108.3 (2)
C32—O35—H35109.5C14—N12—H12109.6
O31—C31—O32123.6 (2)C12—N12—H12109.6
O31—C31—C32120.4 (2)C16—N12—H12109.6
O32—C31—C32116.1 (2)N11—C11—C12109.1 (2)
O35—C32—C31108.1 (2)N11—C11—H11A109.9
O35—C32—C33112.0 (2)C12—C11—H11A109.9
C31—C32—C33113.1 (2)N11—C11—H11B109.9
O35—C32—H32107.8C12—C11—H11B109.9
C31—C32—H32107.8H11A—C11—H11B108.3
C33—C32—H32107.8N12—C12—C11109.9 (2)
C34—C33—C32111.0 (2)N12—C12—H12A109.7
C34—C33—H33A109.4C11—C12—H12A109.7
C32—C33—H33A109.4N12—C12—H12B109.7
C34—C33—H33B109.4C11—C12—H12B109.7
C32—C33—H33B109.4H12A—C12—H12B108.2
H33A—C33—H33B108.0N11—C13—C14108.6 (2)
O33—C34—O34123.1 (2)N11—C13—H13A110.0
O33—C34—C33123.7 (2)C14—C13—H13A110.0
O34—C34—C33113.2 (2)N11—C13—H13B110.0
C44—O44—H44109.5C14—C13—H13B110.0
C42—O45—H45109.5H13A—C13—H13B108.3
O41—C41—O42123.6 (2)N12—C14—C13110.0 (2)
O41—C41—C42120.2 (2)N12—C14—H14A109.7
O42—C41—C42116.2 (2)C13—C14—H14A109.7
O45—C42—C41108.1 (2)N12—C14—H14B109.7
O45—C42—C43110.8 (2)C13—C14—H14B109.7
C41—C42—C43112.7 (2)H14A—C14—H14B108.2
O45—C42—H42108.4N11—C15—C16108.8 (2)
C41—C42—H42108.4N11—C15—H15A109.9
C43—C42—H42108.4C16—C15—H15A109.9
C44—C43—C42111.5 (2)N11—C15—H15B109.9
C44—C43—H43A109.3C16—C15—H15B109.9
C42—C43—H43A109.3H15A—C15—H15B108.3
C44—C43—H43B109.3N12—C16—C15110.1 (2)
C42—C43—H43B109.3N12—C16—H16A109.6
H43A—C43—H43B108.0C15—C16—H16A109.6
O43—C44—O44123.0 (2)N12—C16—H16B109.6
O43—C44—C43123.7 (2)C15—C16—H16B109.6
O44—C44—C43113.3 (2)H16A—C16—H16B108.2
C54—O54—H54109.5C25—N21—C21109.5 (2)
C52—O55—H55109.5C25—N21—C23110.3 (2)
O51—C51—O52123.7 (2)C21—N21—C23109.2 (2)
O51—C51—C52120.4 (2)C25—N21—H21109.3
O52—C51—C52115.9 (2)C21—N21—H21109.3
O55—C52—C51108.2 (2)C23—N21—H21109.3
O55—C52—C53111.3 (2)C24—N22—C26110.2 (2)
C51—C52—C53112.1 (2)C24—N22—C22110.2 (2)
O55—C52—H52108.4C26—N22—C22108.7 (2)
C51—C52—H52108.4C24—N22—H22109.3
C53—C52—H52108.4C26—N22—H22109.3
C54—C53—C52111.6 (2)C22—N22—H22109.3
C54—C53—H53A109.3N21—C21—C22109.3 (2)
C52—C53—H53A109.3N21—C21—H21A109.8
C54—C53—H53B109.3C22—C21—H21A109.8
C52—C53—H53B109.3N21—C21—H21B109.8
H53A—C53—H53B108.0C22—C21—H21B109.8
O53—C54—O54122.5 (2)H21A—C21—H21B108.3
O53—C54—C53124.3 (2)N22—C22—C21109.2 (2)
O54—C54—C53113.2 (2)N22—C22—H22A109.8
C64—O64—H64109.5C21—C22—H22A109.8
C62—O65—H65109.5N22—C22—H22B109.8
O61—C61—O62124.0 (2)C21—C22—H22B109.8
O61—C61—C62120.0 (2)H22A—C22—H22B108.3
O62—C61—C62115.9 (2)N21—C23—C24109.4 (2)
O65—C62—C61108.4 (2)N21—C23—H23A109.8
O65—C62—C63111.2 (2)C24—C23—H23A109.8
C61—C62—C63113.0 (2)N21—C23—H23B109.8
O65—C62—H62108.0C24—C23—H23B109.8
C61—C62—H62108.0H23A—C23—H23B108.2
C63—C62—H62108.0N22—C24—C23109.0 (2)
C64—C63—C62111.8 (2)N22—C24—H24A109.9
C64—C63—H63A109.3C23—C24—H24A109.9
C62—C63—H63A109.3N22—C24—H24B109.9
C64—C63—H63B109.3C23—C24—H24B109.9
C62—C63—H63B109.3H24A—C24—H24B108.3
H63A—C63—H63B107.9N21—C25—C26109.4 (2)
O63—C64—O64122.5 (2)N21—C25—H25A109.8
O63—C64—C63123.8 (2)C26—C25—H25A109.8
O64—C64—C63113.7 (2)N21—C25—H25B109.8
C11—N11—C13110.0 (2)C26—C25—H25B109.8
C11—N11—C15109.3 (2)H25A—C25—H25B108.2
C13—N11—C15109.2 (2)N22—C26—C25108.8 (2)
C11—N11—H11109.4N22—C26—H26A109.9
C13—N11—H11109.4C25—C26—H26A109.9
C15—N11—H11109.4N22—C26—H26B109.9
C14—N12—C12109.8 (2)C25—C26—H26B109.9
C14—N12—C16109.9 (2)H26A—C26—H26B108.3
O31—C31—C32—O357.0 (3)C62—C63—C64—O64131.2 (2)
O32—C31—C32—O35171.1 (2)C13—N11—C11—C1262.9 (3)
O31—C31—C32—C33117.6 (2)C15—N11—C11—C1257.0 (3)
O32—C31—C32—C3364.3 (3)C14—N12—C12—C1156.5 (3)
O35—C32—C33—C3450.2 (2)C16—N12—C12—C1163.6 (3)
C31—C32—C33—C3472.2 (2)N11—C11—C12—N125.5 (3)
C32—C33—C34—O3353.9 (3)C11—N11—C13—C1456.3 (3)
C32—C33—C34—O34126.5 (2)C15—N11—C13—C1463.6 (3)
O41—C41—C42—O457.1 (3)C12—N12—C14—C1363.0 (3)
O42—C41—C42—O45171.2 (2)C16—N12—C14—C1356.1 (3)
O41—C41—C42—C43115.7 (2)N11—C13—C14—N125.7 (3)
O42—C41—C42—C4365.9 (3)C11—N11—C15—C1662.7 (3)
O45—C42—C43—C4449.8 (2)C13—N11—C15—C1657.7 (3)
C41—C42—C43—C4471.5 (2)C14—N12—C16—C1562.3 (3)
C42—C43—C44—O4363.1 (3)C12—N12—C16—C1557.8 (3)
C42—C43—C44—O44115.2 (2)N11—C15—C16—N124.2 (3)
O51—C51—C52—O5513.6 (3)C25—N21—C21—C2257.0 (3)
O52—C51—C52—O55165.8 (2)C23—N21—C21—C2263.9 (3)
O51—C51—C52—C53109.6 (2)C24—N22—C22—C2156.6 (3)
O52—C51—C52—C5371.1 (3)C26—N22—C22—C2164.2 (3)
O55—C52—C53—C5452.3 (2)N21—C21—C22—N225.9 (3)
C51—C52—C53—C5469.1 (2)C25—N21—C23—C2462.1 (3)
C52—C53—C54—O5357.3 (3)C21—N21—C23—C2458.3 (3)
C52—C53—C54—O54121.3 (2)C26—N22—C24—C2357.9 (3)
O61—C61—C62—O659.0 (3)C22—N22—C24—C2362.0 (3)
O62—C61—C62—O65169.3 (2)N21—C23—C24—N223.9 (3)
O61—C61—C62—C63114.7 (2)C21—N21—C25—C2663.4 (3)
O62—C61—C62—C6367.0 (3)C23—N21—C25—C2656.7 (3)
O65—C62—C63—C6450.9 (2)C24—N22—C26—C2563.2 (3)
C61—C62—C63—C6471.3 (2)C22—N22—C26—C2557.6 (3)
C62—C63—C64—O6348.2 (3)N21—C25—C26—N224.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O310.931.792.634 (2)150
N12—H12···O510.931.742.610 (2)154
N21—H21···O610.931.792.631 (2)148
N22—H22···O410.931.772.629 (2)153
O34—H34···O52i0.841.802.611 (2)161
O35—H35···O62ii0.841.882.700 (2)165
O44—H44···O42iii0.841.832.631 (2)160
O45—H45···O32iv0.841.902.709 (2)161
O54—H54···O32v0.841.832.649 (2)166
O55—H55···O42vi0.841.912.732 (2)167
O64—H64···O62vii0.841.802.630 (2)167
O65—H65···O520.841.872.699 (2)169
C12—H12B···O44viii0.992.413.252 (3)143
C15—H15B···O43ix0.992.343.258 (3)154
C22—H22A···O54viii0.992.453.390 (3)158
C23—H23B···O32x0.992.463.391 (3)156
C26—H26B···O33x0.992.283.265 (3)171
Symmetry codes: (i) x, y, z+1; (ii) x, y1/2, z+3/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y, z1; (v) x, y, z+2; (vi) x+1, y1/2, z+1/2; (vii) x, y+1/2, z1/2; (viii) x+1, y, z+1; (ix) x1, y+1/2, z+1/2; (x) x+1, y+1/2, z1/2.
 

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